Women in Business Q&A: Karen Kaplan, Chairman and CEO, Hill Holliday

Laura Dunn
Social Media and Communications Professional, Founder and Editor of Political Style, Director of LED Media, Journalist and Author

Karen Kaplan is Chairman and CEO of Hill Holliday in Boston. A driving force behind Hill Holliday's growth to more than $1 billion in annual billings, she's been recognized by Business Insider and Advertising Age as one of the most influential women in advertising. Karen first joined Hill Holliday as a receptionist in 1982. Karen's leadership has helped build an impressive list of premier clients including Bank of America, Capella University, Celgene, Chili's, Dunkin' Donuts, Harvard Pilgrim Health Care, Johnson & Johnson, John Hancock, LG Home Appliances USA, Liberty Mutual, Merrill Lynch, Novartis, (RED), Smucker's, Supercuts and TJX.

How has your life experience made you the leader you are today?

I grew up in the most gender-neutral household in the world. My mother worked, my father vacuumed. My father worked, my mother did the dishes. Unfortunately, nobody knew how to cook, but that's another story. I grew up in a world where there was work to be done, and who did what just didn't matter. And I believe that point-of-view, that perspective on life, is the greatest inspiration of my life. My parents taught my sister and me that anybody, male or female, could do anything he or she wanted to do. A simple but important concept, and for us, words to live by.

My father was blessed with a natural ability to do anything. A natural athlete, he's always been great at every sport - football, baseball, track, golf. My dad taught me how to ice skate, ski, fish, dive, canoe, play football, tell a joke and juggle. There were no formal lessons, no hired instructors in our house, because my father knew how to do absolutely everything. And he knew how to fix everything. Just sat down and took it apart, then put it right back together again. Washing machines, cars, clocks - he even knew how to take his two occasionally opinionated daughters apart and put them back together with just the right choice of words. He never wanted us to be too impressed with ourselves, reminding us that, "A pat on the back is just six inches from a kick in the butt."

If my father's gift is a natural ability to do anything, my mother's gift is a natural curiosity to learn anything. My mother is the smartest person I know. She knows everything, but she's not a know-it-all. She reads. All the time. Newspapers, magazines, reference books. She reads everything she can get her hands on. And while my mother reads, she watches CNN and CNBC and PBS. My mother never went to college because her parents told her there was no reason for a woman to go to college. But that didn't stop my mother. She has been studying and educating herself for 80 years, 7 days a week, 16 hours a day. My mother told me, every day of my life, that I was special, and that I could do absolutely anything I set my mind to. My mother was my "I believe in you" person. Most successful people have an "I believe in you" person in their lives. I know for a fact that my mother didn't have that person in her life. But she made damn sure that I did.

How has your previous employment experience aided your position at Hill Holliday?

When Jack Connors, Founder of Hill Holliday, hired me as the receptionist back in 1982 he said, "Congratulations, Karen. You are now the face and the voice of Hill Holliday". And the way he framed the job - as the face and the voice of Hill Holliday - really gave me pause. I realized then that this wasn't just some job - this was a big responsibility. And because he took it seriously, I took it seriously. I remember thinking, the face and the voice of Hill Holliday - that sounds pretty important. That sounds like something the CEO should be responsible for. So at that moment, I decided I would consider myself the CEO of the reception desk, and that's how I approached the job. And then, when I was promoted into the next job, I considered myself the CEO of that. And I approached every single job that same way - I considered myself the CEO of every department I ever ran, and every job I ever had. And I've had the same 16 jobs everyone my age has had, I've just been lucky enough to have had them all at the Hill Holliday.

What have the highlights and challenges been during your tenure at Hill Holliday?

So many highlights and challenges come to mind when I reflect on my 32-year tenure at Hill Holliday, but for me what eclipses all the wins and losses has been having the privilege of watching people grow. Our Founder Jack Connors had a rare ability, one that I hope I have developed as well, to see someone not as they used to be, but rather as what they can be. I think there is no greater joy in any business than watching people grow, watching them become more successful than they ever imagined. It's just amazing what happens to people when someone believes in them. They actually start to believe in themselves.

What advice can you offer women who are seeking a career in advertising?

Be curious, open and collaborative. Speak up, be brave, pay attention and be willing to work hard. Don't ever underestimate your ability to think outside the box. Women have a tremendous natural advantage over men when it comes to thinking outside the box because we've never been allowed inside the box, and as a result, we're much better at thinking differently about problems and managing through ambiguity, which aligns very nicely with the challenges in advertising today.

How do you maintain a work/life balance?

I believe "work/life balance" is a flawed concept. People don't have their work life in one silo and their home life in a separate silo, and if what they are trying to achieve is balance, by definition one comes at the expense of the other. To me, it's not a question of trying to balance work and home; it's all one thing called life. I think it's time we reframe the way we think about some of the challenges that go along with having a family and a career in order to really set people up to succeed. We have to judge and measure people not on how, when and where they do their work, but rather on what they accomplish, on the quality of their ideas, and on the impact they make on the agency, on their clients' business and on the community.

What do you think is the biggest issue for women in the workplace?

One of the findings of a recent McKinsey survey was that women are promoted based on performance, whereas men are promoted based on potential. In other words, men are considered for promotion on the basis of what they can bring to the table, while women are considered for promotion on the basis of what they have brought to the table. That means there's a higher hurdle that women have to get over in our careers in order to advance; we have to take more risks and take on tougher assignments to prove ourselves, we always have to deliver because we don't get the benefit of the doubt like men do, we have to be more disciplined and more focused on performance to get to the top. And with apologies to Sheryl Sandberg, I think that it's really important that both men and women "lean in" on the issue of women's leadership - and particularly when it comes to affecting institutional changes that will allow more women to succeed in more corporate environments.

How has mentorship made a difference in your professional and personal life?

I have what I call my own personal board of directors. There are no board meetings, none of my board members is aware of who else is on my board, or even that they're on my board, but without realizing it, each of them has been immensely helpful to me over the years. Like any corporate board, each of them has unique qualifications, attributes and skills, and each of them shares their unique insights and perspectives generously.

What do you want Hill Holliday to accomplish in the next year?

As CEO, my vision for HH is to be the best creatively driven modern agency in the country. This is what every Hill Holliday employee is focused on every day, and every word of this vision is deliberate. Best means the best, not the biggest - quality and quantity are two different things. Creatively driven means creatively driven in the broadest possible sense - creative as in mindset, not as in department. And modern means we are committed to future-proofing our agency and our clients' businesses to always be a step ahead.